How To Woo A Waldorf
by amandajbruce
Summary: Set just prior to Blair's wedding to Louis. While trying to get some writing done, Dan begins 'Love and Loss on the Upper East Side: Your Guide to Wooing a Society Girl.'


**A/N: This was originally written for a fic exchange back in January on an LJ community, but the moderator for the community disappeared, and never posted all of our fics. I decided I've waited long enough, and I'm just going to go ahead and post it here. This is the first story I ever wrote for Gossip Girl, and it might be my last. I found it to be a really strange world to write for. Maybe if something strikes my fancy, I'll revisit it, but who knows?**

* * *

It's one of those things that occurs to Dan while he's staring at a blank word document, willing his brain to begin listing ideas for his new book. And it's spawned by something a homeless man on the corner said to him after witnessing Serena and himgo their separate ways following a quick meet up for coffee.

"Second pretty girl I seen you with this week, boyo. Got any tips for me?" He winked after he asked, as if Dan wouldn't understand the implication. Of course, he also then cackled so much, he hocked up a wad of phlegm the size of Dan's hand, so he just gave the guy a dollar and a nod, and kept walking.

Sitting at his computer now though, it does occur to him that while dating Serena, he was the envy of half the guys on the Upper East Side. And when people thought he was secretly dating Blair, he was the envy of the other half. He wasn't entirely sure how a Lonely Boy from Brooklyn wound up being the object of so many people's jealousy – even a crown prince. It was bewildering, and, though he wouldn't admit it to anyone else, a little empowering. He began to click the keyboard without being conscious of what he outlined. If nothing else, it might turn into a decent short story to hold on to.

_Love and Loss on the Upper East Side: Your Guide to Wooing a Society Girl_

Eh, that title was a tad long. It didn't have the best ring to it either. He would get back to that.

-o-

Step One: Treat Her Like An Equal.

It boggles the mind just how many guys are introduced to a woman on the Upper East Side, and then proceed to simply worship her. Adoration and adulation can only get you so far. These women have housekeepers and drivers for that. They don't need another employee; they need a companion. On the flip side, a guy cannot go around treating a woman of the Upper East Side as though _she_ is the one who is lucky to have _him_. It doesn't matter if he owns his own Empire, or if he lives in a palace, or if he eats stale cereal every day for breakfast in a slightly run down Brooklyn loft. If he expects her to worship him, he won't last long in her good graces.

The trick is maintenance of equal footing. If she pushes, you push back. If she pulls, you pull. It sounds like an exhausting game of tug-of-war, but there will come a point where the two can meet in the middle. The middle, as equals, is ideal.

"_Humphrey, what are you doing?"_

"_Ordering?"_

"_Without even asking? What if I don't like the toppings you pick?"_

"_Blair, you always order the same thing, I think I can handle it."_

"_Maybe I want to change it up this week."_

"_Since when?"_

"_Since now."_

"_Fine, here's the menu. Knock yourself out. The phone's right there."_

"_... when was the last time you disinfected the buttons on your cordless? Dorota wipes our phones down thrice daily to prevent germs spreading... I guess the usual's acceptable today." _

_-o-_

Step Two: Speak Only Truths

If there is one thing an Upper East Sider hates more than a bad photograph, it's being lied to. Brown-nosers and schemers are the most notorious of liars. Where else would you find a group made primarily of those kinds of people, but the wealthiest neighborhoods in New York? Maybe Hollywood, where fake tans and fake body parts are more common than a real marriage. But if a young woman lives on the Upper East Side, chances are she witnesses ten times more lies than the average person on a daily basis. It could be her stepfather wanting an affair with the new nanny kept quiet, or it could be one of the wannabes at school trying to earn brownie points, or it could even be a backstabbing best friend intent on branching out on her own. Regardless of the types of liars the girl in question encounters, she will find the truth refreshing, a welcome change. And as a result, she will also find the guy, that is you, the truth teller, refreshing as well.

"_These garlic knots are amazing. It's almost like they're laced with something to make you keep eating them, you know?"_

"_You must like them, considering you've had four to my one."_

"_I'm not obsessed with watching my girlish figure like you are."_

"_I guess I'm just not that hungry after all."_

"_No, I think it's more likely that you've had five slices over there. Did you think I wouldn't notice that you wolfed one down when I went to get a beer? Or the other one when I had to fix the DVD because it kept skipping? Or-"_

"_Word of advice, Humphrey: stop talking. No girl likes to hear that the guy she's spending time with finds her piggish."_

"_Well, at least you know I don't find you priggish... all the time."_

"_All the time?"_

"_You realize you ruined a perfectly good garlic knot by throwing it at my head, right?"_

"_Just pretend I'm not here. You can still eat it off the couch cushion like a Neanderthal."_

_-o-_

Step Three: But Be Willing To Scheme

As much as she appreciates the truth, scheming is a hallmark of the rich and privileged, and if you want to get into (and take up residence in) her good graces, you have to be willing to play a part in one of her schemes, or even mastermind one yourself. The more complicated the scheme, and the more social ramifications it has, the better. And inevitably, when the scheme comes to light, just like all of the skeletons in all of the giant walk-in closets are eventually wont to do, you will also be there to help repair the rapidly unraveling reputation of yourself and the girl with whom you schemed.

"_There's this new girl working the desk at the Empire on Friday nights."_

"_So? And more importantly, why do you know that?"_

"_Sometimes, I walk aimlessly through the streets, letting my mind wander the way my feet do, and sometimes, I just happen to wander right into the lobby."_

"_What's your point, Blair?"_

"_I think she's trying to use Chuck for his connections. I saw her - "_

"_I thought you were done with this."_

"_What? The spying? The scheming? Or the Chucking?"_

"_All of the above."_

"_Oh, come on, a good scheme is like a good cleanse. It opens the mind and awakens the body."_

"_Until you get caught."_

"_Are you going to help or not?"_

"_What do you need me to do?"_

_-o-_

Step Four: Expect The Unexpected

After you have completed the first three steps, and had plenty of face time with your favorite New Yorker, it might occur to you that you are now one of the people who knows her best. Don't let that fool you though. Because the woman you think you know everything about has yet to show you her true colors. The women on the highest tier of the social pyramid always hold a little of themselves back, and they do the one thing you would never expect, just when you absolutely least expect it. It's best to just accept the surprise and roll with it. What you should really expect is that you will constantly be surprised.

"_Rrrruuupppp. Excuse me."_

"_Wow, you must be feeling really comfortable here. You're acting like a real Brooklyner."_

"_I don't know what you're referring to."_

"_So, I just imagined that?"_

"_Imagined what? Even Waldorfs have normal human bodily functions. Belching is perfectly healthy for your digestive system. You just refrain from doing it in public."_

"_Really? So, you even-"_

"_Humphrey, don't push it."_

_-o-_

Step Five: Know The Vintage

Not just when it comes to wine, though that is important as well if the girl in question is old enough to order from the wine list at all of the chicest establishments. Actually, considering most Upper East Siders have their regular haunts, though they would never refer to them as such, chances are she's had all of the best wines, and all of their grape growing details, committed to memory since she was fifteen. She won't even need the list, or need to show any form of identification. If you do, good luck. She'll either find you incredibly adorable, or incredibly boring, depending on her mood.

But when you've entered this world of high class restaurants and up scale boutiques, it isn't just the year of the wine you need to pay attention to. You better know a modicum about her favorite fashion pieces, designers, and maybe even some historical gossip. The amount of knowledge you will need to maintain would exhaust lesser men.

"_You know, I think Lily owns the scarf that the French mistress wears in this scene."_

"_That's not possible. Only three hundred were made and-"_

"_Half of them were destroyed in a fire on the soundstage for the movie, and the rest of the them were given as gifts to crew members, except for the one worn by the actress. She got to keep it."_

"_Exactly. Color me surprised that you actually know something about such an exquisite piece of fashion artistry."_

"_Yeah, well, I'm pretty sure Lily bought the one used in this scene at a charity auction a couple of years ago."_

"_Is it still that amazing?"_

"_Amazing? It's a scarf."_

"_But I mean, does the color still pop like it does here? Oh, there aren't any tears in the fabric or anything, are there?"_

"_I don't think so. I've only seen it once. It's brighter than it looks on screen, more of a marigold than a canary."_

"_Wow, and you even know your hues. I do believe I'm rubbing off on you."_

_-o-_

Step Six: Go For The Classics

Speaking of history lessons, you might do well to turn to the past for inspiration in your other wooing techniques as well. There's a reason some things are referred to as classics – they never go out of style. And don't just buy a box of chocolates or a bouquet of flowers at the corner market. It pays to know her favorites – brands, businesses, colors. The classics have to be tailored to the girl, or they're simply cliche.

"_Oh, hey-"_

"_Hay is for horses, not people."_

"_Right. I picked something up for you when you called earlier."_

"_Oh?"_

"_I don't know if you'll still want it after all that pizza though."_

"_I wonder what it could possibly be then?"_

"_You don't have to be so sarcastic. Maybe I'll just hang on to it."_

"_Either give it to me or shut up about it. You're interrupting the movie. I might miss something important."_

"_Because between the two of us, we haven't seen this movie more than 100 times? Fine. Here, I know they've turned into your favorite, so... maybe you'll have more room for them later."_

"_Are you serious? There is always room for macaroons."_

_-o-_

Step Seven: Hold Her Hair Back, Or Guard The Door

Let's face it, girls from up in the social stratosphere have a very long way to fall, and there are always plenty of issues to push them closer to the edge. Whether she went out partying and had one too many margaritas last night, or she's had a momentary relapse with a past eating disorder, she has to know that you are there for her. If you can hold her hair back, keep others out of her personal space, and still smile at her afterward, she'll know she can trust you. She'll know that including you in her inner circle wasn't a mistake. Just don't make your own mistake by trying to use one of these moments of weakness against her.

"_You okay in there?"_

"_Fine. Is Nate still here?"_

"_No. He was just making a quick stop. And no, I didn't tell him you were hiding in the bathroom. Are you coming out any time soon?"_

"_Just... watch the movie without me."_

"_I'm not going to leave you locked in my bathroom doing God knows what while I watch the movie you picked."_

"_You act like I'm in here because – oh, no."_

"_You sure you're okay?"_

"_Haven't we been over this before? I'm pregnant, not bulimic. And-"_

"_You're not ready to tell anyone yet, I know. I'll get you a glass of water."_

_-o-_

Step Eight: Be Her Safe Haven

Everyone needs a place they can go to be themselves, to escape the troubles, the stresses, of their everyday life. For a lot of people, they hide in their bedrooms. Little girls will sit on the floor of their mothers' closets. Little boys will curl up under their fathers' desks with their favorite toys. The older you get, and the more people in your house, it can be difficult to truly escape though. Which is why you and your safe haven need to be her safe haven as well. There's only so much of the help peeking their heads into her room to check on her, only so many "well wishing" paparazzi, she can take on a regular basis. Even if you have a torn up couch that smells like onions, it's a place that's just for the two of you, where she can curl into your side and hide from the world for a little bit longer.

"_If I didn't know better, I'd think you were actually starting to like it here. Three movies in one night has got to be a record for us."_

"_There's no 'us', Humphrey."_

"_You know I didn't mean it like that."_

"_Uh huh."_

"_Do you need me to call you a cab?"_

"_No, no, we've still got one more movie left to watch."_

"_It's two in the morning. You sure you want to watch another one? Or are you avoiding going home for some reason?"_

"_What? A girl can't spend a non social Saturday night watching movies with an acquaintance in Brooklyn?"_

"_Blair."_

"_Okay... Dorota keeps fussing over me. She's got all these meal plans and exercise programs and breathing classes she wants me to do, and it's driving me crazy! She's treating me like I'm thirteen years old and am unable to take care of myself."_

"_She does work for you. It is her job to make your life easier..."_

"_But this is different. It's like she's obsessed. Between Dorota and wedding planning, I feel like I can't breathe half the time. I just want a few hours to myself."_

"_With me."_

"_Well... you have good taste in movies and pizza, and your apartment is far enough away from everyone else..."_

"_You can stay as long as you want."_

_-o-_

Step Nine: Be Her Getaway Driver

Have you ever noticed that nine out of every ten people raised on the Upper East Side employ a driver? Or three? Most of them never have to learn to drive a car themselves. Of course, that could be said of most New Yorkers in general, but you'll never catch an Upper East Sider doing something as lamentable as taking the subway – not by choice anyway. They have no problem hailing cabs and forking out the extra money for a private car though; Which is why you should be ready to climb into the driver's seat, should the need arise. Whether she pushes the driver too far and he quits, or she attends an event where she can't get a car at the last minute, or she decides to run away for the weekend. Or, maybe if she decides to rob a bank. But who of the rich and privileged few is going to go out of their way to rob a bank, really?

"_If you had to go away where no one would find you, where would you go?"_

"_Why? You getting cold feet? Thinking about planning an escape route?"_

"_I like to plan for all possibilities. What if I need to get away from the public for a while? Do you think I could hide out in a small town in Iowa or something?"_

"_What would you do in Iowa?"_

"_Farm potatoes or something. I don't know."_

"_You're thinking of Idaho."_

"_Well, London's out. Too_ _rainy."_

"_And you'd need a passport. So nothing outside of North America. And if you don't like the rain, Seattle's out too, then."_

"_Right. And Cabo or Miami or Los Angeles all have too many celebrities. So those are out too."_

"_And you'd probably need someone to drive you, but if you hired a driver, it would have to be someone you'd trust who isn't going to sell your location to anyone."_

"_Then I guess I'd have to hire you. Even Serena's sold me out to Gossip Girl before. Where could we go?"_

"_I would go somewhere in Rhode Island."_

"_Rhode Island?"_

"_Smallest state in the U. S. Not too far away, so I wouldn't need a passport. Nobody would think to look there."_

"_I don't think I've ever been to Rhode Island. We should go sometime."_

"_Yeah... you ever need to get away, you just let me know."_

_-o-_

Step Ten: Find Satisfaction In Friendship

Because that's the thing about an Upper East Side girl, isn't it? With as particular as they are, as refined as their tastes, and as quick as their rush to judgment can be, the truth is, all your efforts at courtship might be for naught. No matter how perfect you might be for one another, she just might not be able to see it. And if you love her, you will be able to understand that. Because all of the reasons that you love her are the same reasons informing her decision to love someone else. You _can _be her soulmate, even if you _can't _be the love of her life; at least, not until she's ready to see that. And that could very well require a whole lot of friendship, and a whole lot of waiting.

"_What happened? Is there something wrong with the movie?"_

"_I don't think the movie would make all the lights go out."_

"_Well, do something!"_

"_Blair, I can't see anything. Hold on, let me find my phone... It looks like the lights are out on the whole block."_

"_What am I supposed to do now? I can't finish watching my movie."_

"_We could go to bed – separately, obviously. You can take the bed. I can sleep out here."_

"_I'm not tired yet."_

"_We could talk?"_

"_What do you want to talk about, Humphrey?"_

"_You tell me. How's the wedding planning going?"_

"_Fine. There are still a few details to work out, but I'll have Dorota help me handle it. I think you've done enough on the wedding front. What else?"_

"_Okay... have you thought about what you're going to do about school after the wedding?"_

"_Why do you always pick topics I don't want to discuss?"_

"_You have to talk about them with someone. Why not me?"_

"_How's your novel going?"_

"_Maybe we should just sit here quietly and wait for the power to come back on."_

_-o-_

It's only when he's done with all of his rough outlining and reminiscing that Dan realizes his list is oddly specific. It doesn't really matter how often he tells Chuck and Nate that he's not in love with Blair, that all they have is friendship, because the truth is, Blair pretty much occupies his every waking moment. But since they've become so close again, and since she forgave him for his use of her likeness in his last novel, he made a promise, that he would not cast her in another heroine role without her permission.

He deftly stabs the 'ctrl' and the 'a,' readying himself to make the notes typed on the screen disappear into technical oblivion. He kind of wishes he could make his own feelings disappear just as easily, but if he hasn't had any luck in the last year, he doubts that he will suddenly gain some now. A knock at the door interrupts his thought process though, a knock he would recognize anywhere. It's delicate, but purposeful, obviously belonging to a woman who knows exactly what she's there for. With a heavy sigh, but an accompanying warm smile, he presses the 'backspace' and watches the document become blank before his very eyes. Rising from his seat, Dan braces himself for another knock, but it doesn't come until he's already reaching the door and twisting the deadbolt.

"Are you making a run for it? Do I need to pack a bag?"

"Very funny, Humphrey. I thought I could have one more movie night in Brooklyn before I'm a married lady. It probably won't be the same when we have to do it in the palace."

She dangles the plastic jacket of the DVD casing from two fingertips as though she's afraid to hold on to it too tightly. Her hair is long and loose, and she's wearing one of those high waisted sundresses and a coat she was favoring to hide the baby bump she doesn't have anymore. He doesn't think she's wearing any makeup though, almost as though she's attempting to go incognito one last time.

"Sure, come on in."

The smile fades from his face when he holds the door open for her and steps out of the way. It didn't really occur to him before this very moment that movie nights, full of gourmet pizza and, in Blair's words, cheap alcohol, would stop once she married Prince Louis. He has known for a very long time that things between them, that a lot of things in New York in fact, would change drastically. But the movie nights, the being alone with Blair in the little bubble that is his Brooklyn loft, he had never allowed those to be added to the "things that will change when Blair is officially a princess" list he had been keeping in his head. He doubts Louis is going to want him flying to Monaco just because Blair wants someone to watch a classic film with, and the time difference is going to make watching via telephone dicey at best.

It's Blair who pops the movie in, grabs them a couple of drinks, and orders the pizza like she lives there. She even props her feet up on the coffee table and leans into Dan like they're a couple of teenagers on a date. Dan tries not to notice, but it's difficult when her head is propped just under his chin, her arm pressed against his chest, her hair tickling his nose. He can feel it every time she breathes, and he wraps his arms around her, waiting for her to admonish him for the contact, but she doesn't. She just takes in another deep breath, inhaling almost through his flannel shirt.

"You smell like onions," she mumbles jokingly against him, and he can feel the heat of her smile even though he can't see it.

"You secretly like onions."

"I guess they aren't so bad."

They don't move from that position until the pizza gets there, and even then, Dan just puts the box on the coffee table; neither of them take a slice, and they quickly settle into their earlier seats all over again.

"This is nice," Blair whispers when the movie's credits are rolling. It's not something she would have said when they first started having these nights to themselves, and Dan wonders if she's thinking that this might be the last time as well. She slides her arm further across his body and holds him in a tight embrace that he returns. "We'll still do this once I'm married, right? Just you, and me, and the pizza?"

And because Dan loves her, even if he hasn't said it aloud, he tells her, "of course we will. You can't get rid of me just because I'm a peasant and you're a princess." He kisses the top of her head. "You'll always have me, whether you want me or not. We'll even do this with your royal children one day, teach them what a good film really is."

Blair is silent for a few minutes, as though absorbing what he said to her, and he worries that talking about children might upset her. She doesn't comment on that part of his statement though. "Good." And then, "can we watch the movie one more time? I'm not ready to go yet."

And because Dan loves her, he pushes play again, and strengthens his resolve to wait out his feelings, and just keep helping to make Blair happy. All his steps to wooing an Upper East Side woman aside, her happiness is all that matters now. And one day, maybe she'll see that. Of course, the way she's holding on to him tonight, and the reluctance she has to leave the comfort of a loft in Brooklyn might suggest that a part of her already does.

-o-


End file.
